Patent GB-1176496-A (GB)
Title: Novel Nitrogen-Containing Phosphonates and Derivatives thereof
Inventor: DOMOVS KELVIN B
IPC: D06M13/288
Filed: 1967-02-21
Abstract: 1,176,496. Nitrogen-containing phosphonates. J. P. STEVENS & CO. Inc. 21 Feb., 1967, No. 8146/67. Heading C2C. [Also in Division C3] The invention comprises nitrogen-containing phosphonates of the formula wherein (a) R is hydrogen or C 1-4  alkyl, (b) Q is a grouping selected from where n is 0 to 2, R<SP>1</SP> and R<SP>11</SP> are selected from H, C 1 -C 4  alkyl, halogen and halo (C 1 -C 4 ) alkyl, X<SP>1</SP> is the grouping -(NH)dN(R<SP>111</SP>)(R<SP>IV</SP>) wherein X<SP>11</SP> is halogen or is -CH(R).P(O) (OR) 2 , -P(O)(OR) 2  or -(NH)dN(R<SP>111</SP>)(R<SP>IV</SP>), d is 0 to 1, R is H or C 1 -C 4  alkyl, R<SP>111</SP> and R<SP>IV</SP> are H, alkyl, hydroxyalkyl, alkoxyalkyl, poly- (alkyleneamino) alkyl, poly-(alkyleneoxy) alkyl, aminoalkyl, alkanoyl, -C(O)OG, -C(O)OAlkylene OH, -C(O)NH 2 , -C(O)NH.CH 2 OH, -C(O)N(CH 2 OH) 2 , -C(O)NHG, C(O)N- (CH 2 OH)G wherein G is C 1 -C 5  alkyl, amidino, hydroxymethylamidino, or bis-(hydroxymethyl amidino, or phosphinylidene(-P(O)) or R<SP>IV</SP> and   R<SP>111</SP> can together with the N atom form a heterocyclic ring, (c) Y<SP>1</SP> is a group of the formula wherein n, R<SP>1</SP>, R<SP>11</SP> and X<SP>11</SP> are as defined above, (d) m is 0 to 3, and (e) Z is selected from the radical Q as defined above, X<SP>1</SP>, -CH(R)X<SP>1</SP> (wherein R and X<SP>1</SP> are as defined above, the grouping and the grouping wherein n, R, R<SP>1</SP>, R<SP>11</SP> and X<SP>11</SP> are as defined above. They may be obtained by reacting appropriate halogenalkyl phosphonates with appropriate nitrogen-containing compounds containing an amino or substituted amino group, e.g. ammonia, primary or secondary amines, hydrazine, substituted hydrazines, alkylenediamines, hydroxyalkylalkylene diamines, hydroxyalkyl amines, heterocyclic amines, e.g. morpholine, pyrrolidine, piperazine, alkyleneimines, amides, e.g. urea and amidines, e.g. guanidine, and the products especially those derived from urea and guanidine can be methylolated by means of formaldehyde. If desired, the halogenated phosphonate starting material may first be modified by reaction with an appropriate amount of a trialkyl phosphite to yield a halodiphosphonate prior to reaction with the nitrogen-containing compound. The products may also be obtained by reacting a nitrogen-containing phosphonate of the general formula wherein (a) Q<SP>1</SP> is a grouping selected from and (b) Z<SP>1</SP> is selected from Q<SP>1</SP>, -NH(R<SP>111</SP>) and CH(R).NH(R<SP>111</SP>) or is one of the groups and and (c) R ,  R<SP>1</SP>, R<SP>11</SP>, R<SP>111</SP>, X<SP>11</SP>, m and n are as defined above with a compound selected from phosphorus oxychloride, an alkyl isocyanate, a cyclic carbonate, chloroformic acid ester and acyl chlorides. When phosphorus oxychloride is reacted with an aminophosphonate of the above formula the product is a phosphoramidepolyphosphonate in which #PO replaces H at the amino rates on the amino phosphonates, a product of this type being the compound which can be obtained by reacting with POCl 3  the product obtained by replacing the halogens of bis - (2 - chloroethyl)(2 - chloroethyl) phosphonate with the ethylenediamine radical. The products can be reacted with various polyfunctional compounds to form cross-linked phosphorus-containing resins and may be used either alone or in conjunction with such polyfunctional compounds for flame-proofing polymeric material, especially cellulosic material or for enhancing the dyeability of polymeric material, e.g. polyolefines.